Studies on N-Activation for the Lipase-Catalyzed Enantioselective Preparation of [beta]-Amino Esters from 4-Phenylazetidin-2-one

The effect of N-substitution was examined for the enantioselective lipase-catalyzed ring-opening reaction of racemic 4-phenylazetidin-2-one with methanol in dry organic solvents. Marked differences in the reactivity of various N-protected 4-phenylazetidin-2-ones were observed. Preparative-scale reac...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2015; no. 7; p. 1500
Main Authors Sundell, Riku, Kanerva, Liisa T
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.03.2015
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Summary:The effect of N-substitution was examined for the enantioselective lipase-catalyzed ring-opening reaction of racemic 4-phenylazetidin-2-one with methanol in dry organic solvents. Marked differences in the reactivity of various N-protected 4-phenylazetidin-2-ones were observed. Preparative-scale reactions with Candida antarctica lipase B (Novozym 435 preparation) yielded N-acylated methyl (R)-3-amino-3-phenylpropanoates with enantiomeric excess (ee) values >99% in up to a 49% isolated yield, whereas Thermomyces lanuginosus lipase (Lipozyme TM IM) gave enantiomerically enriched methyl (S)-3-acetamido-3-phenylpropanoate. Candida antarctica lipase A catalyzed the cleavage of the N-chloroacetyl protective group, whereas all of the other examined lipases underwent the ring-opening reaction.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201403467